This March 23, 2008 photo provided by the Hennepin County, Minn. Sheriff's Office shows Douglas McAuthur McCain. On Tuesday, Aug. 26, 2014, a U.S. official said McCain, a U.S. citizen, is believed to have been killed in Syria and was there to fight alongside a terrorist group, most likely the Islamic State. (AP Photo/Hennepin County, Minn. Sheriff's Office)

WASHINGTON — Like many teenage boys who grew up in the Midwest in the 1990s, Douglas McAuthur McCain was a fan of Michael Jordan and the Chicago Bulls and played basketball himself as he shuttled between two high schools in suburban Minneapolis.

It was a rootless existence, and in the next 10 years, he was arrested or received citations eight times on charges including theft, marijuana possession and driving without a license.

McCain moved back and forth from New Hope to San Diego and then abroad, where records of his movements ran cold.

Officials now know he ended up in Syria, where three days ago, McCain, 33, became the first American to die while fighting for the Islamic State group.

McCain reportedly was born in Illinois and moved to Minnesota in the 1990s. He was a student in the Robbinsdale Area School District from September 1997 to June 2000, according to Latisha Gray, a spokeswoman for the district.

He attended both Robbinsdale Cooper High School and Robbinsdale Armstrong High School during that period, though district records do not show him graduating from either school.

“We are shocked to learn that a former district student was allegedly involved in this tragic story,” the district said.

His death is one of the first clues U.S. officials have as they try to identify the Americans who have joined a group that has vowed to remake the Middle East. And his death is evidence that the Islamic State is willing to use Americans on the battlefield in the Middle East rather than sending them back to the United States to launch attacks, as Western officials have feared.

“His death is further evidence that Americans are going there to fight for ISIS rather than to train as terrorists to attack at home,” said Richard Barrett, a former British intelligence office, who is now a vice president at the Soufan Group, a security consultancy in New York.

“Nor does it appear that ISIS regards Americans as assets that are too valuable to risk on the front line rather than to keep in reserve for terrorist attacks or propaganda purposes,” he said, using an acronym for one of the militant group’s names.

Federal authorities learned that McCain had traveled to Syria only after he arrived in the country, according to senior U.S. officials. In response, the U.S. authorities included him on a watch list of potential terrorism suspects maintained by the federal government.

McCain was killed over the weekend by anti-Assad rebels backed by the United States and known as the Free Syrian Army. In that battle, the rebels beheaded six Islamic State fighters — but not McCain — and then posted the photographs on Facebook.

It is not clear how McCain was recruited by the Islamic State and traveled to Syria. According to his Facebook page, he traveled to Canada and Sweden last year. Many Americans and Europeans who have ended up in Syria have disguised their travel by passing through other countries before heading to Turkey and crossing into Syria.

On a Twitter account that the authorities believe to be McCain’s, he said he converted to Islam 10 years ago and it was the “best thing” that had ever happened to him.

In a posting June 9, he told someone who appeared to be an Islamic State member that he would soon be joining them. Shortly thereafter, he posted that he was “with the brothers now.”

At an apartment complex in New Hope, Shelly Chase remembered McCain as a friendly boy who welcomed her 9-year-old son, Isaac, when the Chase family moved in about two decades ago. Even though McCain was a few years older, the boys used to lift weights, hit punching bags and play basketball together.

Shelly Chase and her son, now 28, fought back tears as they remembered McCain.

“I’m holding in the tears, I really am, because this is hard. He was a good kid,” Shelly Chase said. “Someone must have persuaded him.”

The Obama administration confirmed McCain’s death.

“We continue to use every tool we possess to disrupt and dissuade individuals from traveling abroad for violent jihad and to track and engage those who return,” said Caitlin Hayden, a spokeswoman for the National Security Council.

The fight in which McCain was killed occurred in the northern city of Marea, where the Islamic State and rebels had been fighting for control in recent weeks, the Free Syrian Army said.

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